Nature leverages densely packed, high aspect ratio surface structures to moderate surface attachment. For example, the helically coiled geometry of rod-like bacterial pili allows the microorganisms to maintain surface attachment even when subjected to high rates of flow through plastic deformation. While many synthetic systems have sought to replicate these high aspect ratio structures, stiff, inflexible micro- and nanopillar surfaces are frequently limited in their aspect ratios by capillary forces. In this work, we develop and characterize high aspect ratio (100,000) arrays of flexible mesoscale polymer ribbons. These thin, filamentous mesoscale polymer ribbons offer numerous advantages over existing systems, including environmentally tunable 3D geometries, entanglements with proximal ribbons, and numerous material compositions. In this dissertation, we explore methods to fabricate and characterize pili-inspired mesoscale polymer ribbon arrays and elucidate key properties of their morphology and mechanics. We fabricate mesoscale polymer ribbon arrays through flow coating, and then visualize their 3D morphology using confocal microscopy. We identify individual ribbon positions in 3D space using computational image analysis techniques adapted from fiber composite materials and calculate key quantitative descriptors to directly compare morphological changes across samples and environmental conditions. We demonstrate and provide a scaling relationship for the decrease in ribbon curvature over time due to surface tension-induced creep. We show that drag forces dominate any morphological changes that may arise from changes to the environment’s pH. Through microcantilever bending, we measure the stress-strain curve and modulus of single mesoscale polymer ribbons and demonstrate their sensitivity to confinement effects. We showcase that mesoscale polymer ribbon arrays tangled about a cantilever follow a load-sharing model, and that the failure of the array is sensitive to both the strength of each individual ribbon and the strength of the ribbon-cantilever grip. Coating the cantilever tip with adhesive polydimethylsiloxane can improve adhesion at the ribbon-cantilever interface. Mesoscale polymer ribbons even exhibit collective wrapping behavior about droplets of perfluorodecalin. These results outline key design parameters for engineering at the mesoscale, which brings mesoscale polymer ribbon arrays closer to applications as adhesives and filters.